Journal
TETRAHEDRON
Volume 84, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2021.132029
Keywords
Asymmetric catalysis; Michael addition; 2,3-Dihydrofurans; Cyclization; Pyrrole; Chiral Ni(II) complex
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Funding
- Russian Science Foundation, Russia [18-13-00447]
- Russian Ministry of Science and Higher Education, Russia [0778-2020-0005]
- Russian Science Foundation [18-13-00447] Funding Source: Russian Science Foundation
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A highly efficient strategy for the enantio- and diastereoselective synthesis of 4,5-dihydrofuran derivatives was developed, resulting in good yields with moderate to high enantioselectivities (84-99% ee) and excellent diastereoselectivities (dr >99%).
A highly efficient strategy for the enantio- and diastereoselective synthesis of 4,5-dihydrofuran derivatives was developed. Addition of carbonyl compounds which contain bulky adamantyl substituent and beta-keto or phosphonate group to conjugated alpha-bromonitroolefins in the presence of a chiral Ni(II) complex gave corresponding non-racemic products of Michael reaction. These adducts were used for intramolecular cyclization leading to trans-4,5-dihydrofurans with two stereocenters. Resulting trans4,5-dihydrofurans were obtained in good yields with moderate to high enantioselectivities (84-99% ee) and excellent diastereoselectivities (dr >99%). (c) 2021 Elsevier Ltd. All rights reserved.
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